NMR and IR Spectroscopy for the Structural Characterization of Edible Fats and OilsMolly W. CrowtherThis article describes an upper-level instrumental laboratory for undergraduates that explores the complementary nature of IR and NMR spectroscopy in the analysis of five edible and structurally similar fats and oils for average chain length, degree of unsaturation, and trans fat content.Crowther, Molly W. J. Chem. Educ.2008, 85, 1550.

Consumer Chemistry |

Food Science |

IR Spectroscopy |

NMR Spectroscopy |

Qualitative Analysis |

Spectroscopy |

Fatty Acids

The Synthesis of a Cockroach PheromonePatty L. FeistThis paper describes the synthesis of gentisyl quinone isovalerate or blattellaquinone, a sex pheromone of the German cockroach and a compound with real-world applications. The experiment also affords students practice in extraction as well as IR and NMR spectroscopy.Feist, Patty L. J. Chem. Educ.2008, 85, 1548.

Esters |

IR Spectroscopy |

Natural Products |

NMR Spectroscopy |

Oxidation / Reduction |

Synthesis

The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder ReactionXavier Sauvage and Lionel DelaudeCharacterization of the product of this organic synthesis through IR and NMR data analysis provides valuable material to familiarize students with different types of protonproton coupling patterns and their typical ranges, serves to illustrate the concepts of green chemistry and atom efficiency, and can be used to exemplify structural analysis and computational studies.Sauvage, Xavier; Delaude, Lionel. J. Chem. Educ.2008, 85, 1538.

A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry LaboratoryEric Eby and S. Todd DealThis alternative, electrophilic aromatic substitutionan iodination reaction of salicylamide, a popular analgesicuses environmentally friendly reagents and serves as a guided-inquiry experiment in which students are asked to predict the orientation of the substitution reaction and determine the product's structure using FT-IR spectroscopy.Eby, Eric; Deal, S. Todd. J. Chem. Educ.2008, 85, 1426.

Aromatic Compounds |

Constitutional Isomers |

Electrophilic Substitution |

Green Chemistry |

IR Spectroscopy |

Synthesis

Synthesis of the Commercial Antidepressant Moclobemide Jesse D. MoreDescribes an experiment for the undergraduate organic chemistry laboratory in which students synthesize the commercial antidepressant drug moclobemide, marketed under the trade name Manerix, in one step using commercially available material. The purity and identity of the product are confirmed by melting point and NMR and IR spectroscopy.More, Jesse D. J. Chem. Educ.2008, 85, 1424.

Drugs / Pharmaceuticals |

IR Spectroscopy |

Medicinal Chemistry |

NMR Spectroscopy |

Synthesis

The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR DyeCheryl M. MascarenhasIn this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting.Mascarenhas, Cheryl M. J. Chem. Educ.2008, 85, 1271.

Alcohols |

Aromatic Compounds |

Dyes / Pigments |

Esters |

IR Spectroscopy |

NMR Spectroscopy |

Synthesis |

Thin Layer Chromatography |

UV-Vis Spectroscopy

The Preparation and Enzymatic Hydrolysis of a Library of EstersElizabeth M. Sanford and Traci L. SmithIn this investigative case study, students work collaboratively to prepare and characterize a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver and orange peel esterases.Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ.2008, 85, 944.

Peer Mentoring in the General Chemistry and Organic Chemistry LaboratoriesCaleb A. Arrington, Jameica B. Hill, Ramin Radfar, David M. Whisnant, and Charles G. BassThis article describes a discovery experiment in which organic chemistry students act as mentors to general chemistry students. Members from both groups work together to isolate an unknown compound using distillation. The structure of the product is then determined collaboratively using IR and NMR spectroscopy.Arrington, Caleb A.; Hill, Jameica B.; Radfar, Ramin; Whisnant, David M.; Bass, Charles G. J. Chem. Educ.2008, 85, 288.

IR Spectroscopy |

NMR Spectroscopy

ATR–FTIR Spectroscopy in the Undergraduate Chemistry LaboratoryJennifer D. Schuttlefield and Vicki H. GrassianPresents several examples of the use of attenuated total reflectance-Fourier transform infrared spectroscopy in the undergraduate chemistry laboratory, including measuring the infrared spectra of solid and liquid organic compounds commonly used as unknowns and of inorganic solids synthesized by students.Schuttlefield, Jennifer D.; Grassian, Vicki H. J. Chem. Educ.2008, 85, 279.

IR Spectroscopy |

Liquids |

Qualitative Analysis |

Quantitative Analysis |

Solids |

Undergraduate Research

Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-MethylstyreneBrad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. MurphyIn the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition. Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ.2008, 85, 102.

Addition Reactions |

Alcohols |

Alkenes |

Constitutional Isomers |

IR Spectroscopy |

Microscale Lab |

NMR Spectroscopy |

Synthesis

Synthesis of Quaternary Ammonium Salts of Tricyclic Cationic Drugs: A One-Pot Synthesis for the Bioorganic Chemistry LaboratoryLinda S. Brunauer, Abid C. Mogannam, Won B. Hwee, and James Y. ChenDescribes a one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms for a widely used bioactive drug, chlorpromazine, a phenothiazine-based antipsychotic. The conversion of parent drug to the methylated form was evaluated by qualitatively measuring its ability to induce alterations in the shape of mammalian erythrocytes.Brunauer, Linda S.; Mogannam, Abid C.; Hwee, Won B.; Chen, James Y. J. Chem. Educ.2007, 84, 1992.

A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave ConditionsA. Gilbert CookThe product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.Cook, A. Gilbert. J. Chem. Educ.2007, 84, 1477.

Aldehydes / Ketones |

Conformational Analysis |

Gas Chromatography |

IR Spectroscopy |

Mass Spectrometry |

Mechanisms of Reactions |

NMR Spectroscopy |

Stereochemistry |

Synthesis

A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl CompoundsRobert E. RosenbergStudents teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones. Rosenberg, Robert E. J. Chem. Educ.2007, 84, 1474.

Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic DrugEvangelos Aktoudianakis, Rui Jun Lin, and Andrew P. DicksDescribes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ.2006, 83, 1832.

Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-BromobenzoateEric J. Mahan and Mary Alice NadingBefore beginning an experiment, students are told that someone might have sabotaged their experiment to produce other-than-expected results. The objective is to perform the experiment, determine if any sabotage has occurred, and, if so, identify the changes that were made to the reagents as well as the person responsible.Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ.2006, 83, 1652.

Alcohols |

Carboxylic Acids |

Esters |

IR Spectroscopy |

NMR Spectroscopy |

Mass Spectrometry |

Synthesis

Astrochemistry Examples in the ClassroomReggie L. HudsonIn this article some recent developments in astrochemistry are suggested as examples for the teaching of acid-base chemistry, molecular structure, and chemical reactivity. Suggestions for additional reading are provided, with an emphasis on readily-accessible materials.Hudson, Reggie L. J. Chem. Educ.2006, 83, 1611.

Stereospecific Synthesis of the Geometrical Isomers of a Natural ProductT. Grove, D. DiLella, and E. VolkerPresents an experiment for the synthesis of (Z) and (E) isomers that is presented to students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. Molecular modeling is used to explore the conformation of and energy difference between isomers.Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ.2006, 83, 1055.

Synthesis of Methyl Diantilis, a Commercially Important FragranceWilliam H. Miles and Katelyn B. ConnellDescribes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, and provides an excellent introduction to intellectual property laws. Miles, William H.; Connell, Katelyn B. J. Chem. Educ.2006, 83, 285.

Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal AcetylenesWilliam D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. LindbergIn keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ.2005, 82, 1833.

Catalysis |

Heterocycles |

Alkynes |

IR Spectroscopy |

NMR Spectroscopy |

Reactions |

Thin Layer Chromatography |

Synthesis

Presumptive and Confirmatory Drug TestsCraig AndersonTests for illegal drugs were performed on unknowns obtained from over-the-counter cold medicines. Substances that tested positive for the qualitative Marquis color test were found to be false positives for illegal substances, while scopolamine hydrochloride shows a false positive for cocaine hydrochloride with the cobalt thiocyanate reagent. Anderson, Craig. J. Chem. Educ.2005, 82, 1809.

A GC–MS Analysis of an SN2 Reaction for the Organic LaboratoryMalgorzata M. Clennan and Edward L. ClennanThis experiment utilizes an SN2 reaction between an alkyl bromide and potassium acetate to introduce the use of mass spectrometry for structural identification. It also provides students with experience in organic synthesis, the use of IR to identify functional groups, and the use of gas chromatography and response factors to determine product ratios. Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ.2005, 82, 1676.

IR Spectroscopy |

Mass Spectrometry |

Synthesis |

Chromatography |

Esters |

Mechanisms of Reactions |

Microscale Lab |

Gas Chromatography

Preparation, Analysis, and Characterization of Some Transition Metal Complexes—A Holistic ApproachKristy M. Blyth, Lindsay R. Mullings, David N. Phillips, David Pritchard, and Wilhelm van BronswijkIn this laboratory procedure, a wide range of complexes are characterized by IR and UVvis spectroscopy, magnetochemistry, and conductance. The results allow one to the deduce the nature and strength of the bonding of the ligand to the central atom and the number of ions that the complex produces in aqueous solution.Blyth, Kristy M.; Mullings, Lindsay R.; Phillips, David N.; Pritchard, David; van Bronswijk, Wilhelm. J. Chem. Educ.2005, 82, 1667.

IR Spectroscopy |

Magnetic Properties |

UV-Vis Spectroscopy |

Coordination Compounds |

Qualitative Analysis |

Synthesis |

Conductivity

Cotton Effect in Copper–Proline Complexes in the Visible RegionVictor Volkov and Rolf PfisterThis article suggests taking advantage of the visible dd electronic transition of Cu2+, which allows one to contrast the normal optical rotatory dispersion response of d- and l-proline in aqueous solution with the strong Cotton effect observed when these amino acids are complexed with a metal cation.Volkov, Victor; Pfister, Rolf. J. Chem. Educ.2005, 82, 1663.

Chirality / Optical Activity |

IR Spectroscopy |

Molecular Properties / Structure |

Spectroscopy |

Stereochemistry |

UV-Vis Spectroscopy |

Amino Acids |

Coordination Compounds |

Crystal Field / Ligand Field Theory

Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximideMarsha R. Baar and Kristin Wustholzendo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride. Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ.2005, 82, 1393.

Asymmetric Synthesis |

Microscale Lab |

Stereochemistry |

Addition Reactions |

Alkenes |

IR Spectroscopy |

NMR Spectroscopy

Monoterpene Unknowns Identified Using IR, 1H-NMR, 13C-NMR, DEPT, COSY, and HETCORLisa T. AltyThis set of NMR experiments can be a capstone experience for a spectroscopy or advanced laboratory course following organic chemistry. Students are given a monoterpene to identify using IR, 1H-NMR, 13C-NMR, and DEPT data. Once the unknown is identified, they can fully interpret and assign each carbon and each proton signal to the structure using COSY and HETCOR along with the one-dimensional NMR data. The rigidity of the ring systems and the chiral centers in all of the compounds present diastereotopic hydrogens and, in some cases, diastereotopic methyl groups. Alty, Lisa T. J. Chem. Educ.2005, 82, 1387.

Natural Products |

NMR Spectroscopy |

Diastereomers |

Chirality / Optical Activity |

IR Spectroscopy |

Undergraduate Research

Organic Spectroscopy Laboratory: Utilizing IR and NMR in the Identification of an Unknown SubstanceNeil M. Glagovich and Timothy D. ShineAn undergraduate organic laboratory designed to teach the use of IR and NMR spectra interpretation in the identification of an unknown substance has been developed. This laboratory requires the student to obtain the IR spectrum of an unknown substance and, from the interpretation of that spectrum, determine which of several possible functional groups is present in the molecule. Using this information and either the melting point or boiling point of the unknown, the student is able to determine a list of likely candidates (usually between eight and twelve suspects collated from a supplied table of possible compounds). The student will then draw the structures for all candidate compounds and, from those structures, predict the 1H- and 13C-NMR spectra for each.Glagovich, Neil M.; Shine, Timothy D. J. Chem. Educ.2005, 82, 1382.

Generation, Isolation, and Characterization of a Stable Enol from Grignard Addition to a Bis-Ester. A Microscale Experiment for the Undergraduate Organic Chemistry LaboratoryOlivier J.-C. Nicaise, Kyle F. Ostrom, and Brent J. DalkeA microscale experiment for the undergraduate organic chemistry laboratory that consists of preparing and characterizing an alpha-ketoester and its corresponding, remarkably stable enol form, has been developed. The reaction is that of a Grignard reagent with a bis-ester. A difference in reaction temperature is responsible for the selective generation of the alpha-ketoester and the enol ester. Analysis of spectral data (1H NMR and IR) and a knowledge of organic reactions allows the students to determine the detailed structure of the two reaction products and also to suggest a mechanism for their formation. This experiment introduces students to the concept of stability of the tetrahedral intermediate in acyl-transfer reactions. It also gives them a taste of the unexpected. Nicaise, Olivier J.-C.; Ostrom, Kyle F.; Dalke, Brent J. J. Chem. Educ.2005, 82, 1059.

IR Spectroscopy |

Mechanisms of Reactions |

Microscale Lab |

NMR Spectroscopy |

Organometallics |

Reactive Intermediates |

Synthesis

The Ethylene Ketal Protecting Group Revisited: The Synthesis of 4-Hydroxy-4,4-diphenyl-2-butanoneMarsha R. Baar, Charles E. Russell, and Kristin L. WustholzThe multistep synthesis of 4-hydroxy-4,4-diphenyl-2-butanone from ethyl acetoacetate illustrates the use of a ketal protecting group. Reaction of ethyl acetoacetate with ethylene glycol with p-TsOH in toluene produced the ketal ester. Reaction of the crude ketal ester with two equivalents of phenyl magnesium bromide followed by an aqueous acid workup generated the tertiary alcohol and simultaneously removed the ketal protecting group to produce the hydroxyketone. Our procedure is a modification of a previously published synthesis whose end product was 4,4-diphenyl-3-buten-2-one, the dehydrated analog. Baar, Marsha R.; Russell, Charles E.; Wustholz, Kristin L. J. Chem. Educ.2005, 82, 1057.

Synthesis |

Grignard Reagents |

IR Spectroscopy |

Mechanisms of Reactions |

NMR Spectroscopy

Formation of α-Tetralone by Intramolecular Friedel–Crafts AcylationMichael S. Holden, R. David Crouch, and Kathryn A. BarkerA microscale procedure is described for the formation of the industrially-important compound alpha-tetralone. This is an example of an intramolecular FriedelCrafts acylation, utilizing 4-phenylbutanoic acid and a proton source. The title reaction demonstrates the concept of ring-forming reactions and highlights the use of carboxylic acids as an electrophile precursor in electrophilic aromatic substitution reactions. Holden, Michael S.; Crouch, R. David; Barker, Kathryn A. J. Chem. Educ.2005, 82, 934.

Aromatic Compounds |

Microscale Lab |

Synthesis |

Carboxylic Acids |

IR Spectroscopy |

NMR Spectroscopy

Analog Spectrophotometers in the Digital Age: Data Acquisition on a BudgetAlexander Y. Nazarenko and Natalie A. NazarenkoIn this article we describe how to employ an inexpensive analog-to-digital converter and a user interface to Microsoft Excel to make a useful computerized spectrophotometer. Readily available types of data loggers, Vernier LabPro and digital multimeters with an RS-232 interface, were utilized. The proposed design does not compromise the quality of the measurements. The conversion of the data to the Microsoft Excel format makes it a convenient tool for a wide range of data processing applications.Nazarenko, Alexander Y.; Nazarenko, Natalie A. J. Chem. Educ.2005, 82, 294.

The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors LaboratoryChristopher J. Nichols and Melissa R. TaylorA six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column. Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ.2005, 82, 105.

Chirality / Optical Activity |

Chromatography |

IR Spectroscopy |

NMR Spectroscopy |

Synthesis |

Alkenes |

Addition Reactions

Students' Attitudes toward and Conceptual Understanding of Chemical InstrumentationLarry S. Miller, Mary B. Nakhleh, John J. Nash, and Jeanne A. MeyerData collected from field notes, surveys, and interviews are used to evaluate (i) the attitudes students have toward using instrumentation, (ii) how students relate the underlying chemical concepts to the instrumentation, and (iii) how working in a group impacts students' attitudes toward, and their conceptual understanding of, chemical instrumentation. Miller, Larry S.; Nakhleh, Mary B.; Nash, John J.; Meyer, Jeanne A. J. Chem. Educ.2004, 81, 1801.

Chromatography |

Instrumental Methods |

IR Spectroscopy |

Laboratory Equipment / Apparatus

A Discovery-Based Friedel–Crafts Acylation Experiment: Student-Designed Experimental ProcedureAnne McElwee ReeveA discovery-based FriedelCrafts acylation experiment that includes a student-designed procedure, spectroscopic analysis of an unknown aromatic product, and molecular modeling is described. Students design the synthetic procedure and workup for the acylation of an unknown aromatic starting material in an instructor-guided classroom discussion that integrates concepts from the first semester of organic lab into a new context. Reeve, Anne McElwee. J. Chem. Educ.2004, 81, 1497.

Preparation and Investigation of Monodentate and Bridging Pyrazole ComplexesWynne EvansThis practical exercise describes the preparation and characterization of h1-coordinated pyrazole and 3,5-dimethylpyrazole nickel species and the investigation of their reactions with triethylamine. The latter reaction provides a route to preparing a polymer with bridging pyrazolato ligands, coordinating in an exobidentate (N, N?) fashion. We use this experiment, with undergraduate chemistry students, as part of a course providing an introduction to coordination chemistry. The exercise could be extended to take the form of an individual or class project. Suggestions for variations on the described experiment are included. Evans, Wynne. J. Chem. Educ.2004, 81, 1191.

Lewis Acid–Base, Molecular Modeling, and Isotopic Labeling in a Sophomore Inorganic Chemistry LaboratoryChip Nataro, Michelle A. Ferguson, Katherine M. Bocage, Brian J. Hess, Vincent J. Ross, and Daniel T. SwarrComputational methods can be introduced to simulate IR spectra and to view the HOMO of the Lewis base and the LUMO of the Lewis acid. In addition to the computational exercise, NaBD4 can be used in the synthesis of the adduct in place of NaBH4. This allows the students to observe the effect of isotopic labeling on IR spectra. Nataro, Chip; Ferguson, Michelle A.; Bocage, Katherine M.; Hess, Brian J.; Ross, Vincent J.; Swarr, Daniel T. J. Chem. Educ.2004, 81, 722.

Cautionary CommentsJohn J. Esteb and Anne M. WilsonWe never claimed that our procedure would work as written for any alcohol other than the three that we have included.Esteb, John J.; Wilson, Anne M. J. Chem. Educ.2004, 81, 641.

The Separation and Identification of Two Unknown Solid Organic Compounds: An Experiment for the Sophomore Organic Chemistry LaboratoryPatty L. FeistStudents are given a mixture of a solid ketone and a solid alcohol and asked to separate and identify the two components. First the students use TLC to determine the optimum solvent system to separate the two compounds, then they separate the unknowns on a microscale flash chromatography column. The students acquire the melting point, and if possible, the IR and 1H NMR spectra for each separated compound and identify them by matching the observed data with that of known compounds. Feist, Patty L. J. Chem. Educ.2004, 81, 109.

Chromatography |

IR Spectroscopy |

Microscale Lab |

NMR Spectroscopy |

Separation Science |

Qualitative Analysis

Measuring Breath Alcohol Concentrations with an FTIR SpectrometerAdam Kneisel and Michael K. BellamyStudents use aqueous ethanol solutions to make a calibration curve that relates absorbance signals of breath samples with blood alcohol concentrations. Students use their calibration curve to determine the time needed for their calculated blood alcohol levels to drop below the legal limit following use of a commercial mouthwash.Kneisel, Adam; Bellamy, Michael K. J. Chem. Educ.2003, 80, 1448.

Organic Spectroscopy–A Capstone ExperienceJan M. FleischerExperiment requiring students to make decisions regarding the likely structure of their sample based upon an IR spectrum before a final analysis with NMR spectroscopy.Fleischer, Jan M. J. Chem. Educ.2002, 79, 1247.

WebSpectra: Online NMR and IR Spectra for StudentsCraig A. Merlic, Barry C. Fam, and Michael M. MillerWebSpectra is a World Wide Web site at UCLA through which organic chemistry students have convenient access to a library of problems in NMR and IR spectroscopy, ranging in difficulty from introductory to advanced. Students are presented with high-resolution spectra of unknown compounds in addition to the molecular formula. Merlic, Craig A.; Fam, Barry C.; Miller, Michael M. J. Chem. Educ.2001, 78, 118.

Infrared Spectroscopy in the General Chemistry LabMargaret A. HillThree laboratory exercises in which students learn to interpret infrared spectra for simple structural identification. A polymer identification lab uses familiar household polymer samples and teaches students how to use infrared spectral data to determine what bond types are present in the polymers. In a second lab, students learn to prepare potassium bromide pellets of fluorene derivatives and identify them by their functional group differences. The final exercise combines IR with several other lab techniques to identify an organic acid from a field of fourteen possibilities.Hill, Margaret A. J. Chem. Educ.2001, 78, 26.

Instrumental Methods |

IR Spectroscopy |

Molecular Properties / Structure

A Microscale Oxidation PuzzleMichael W. Pelter, Rebecca M. Macudzinski, and Mary Ellen PassarelliWe have adapted oxidation of an alcohol with sodium hypochlorite solution to a "puzzle" approach by using a diol as the substrate for oxidation. The diols under investigation have both a primary and a secondary hydroxyl group. The assignment is to perform the reaction and determine the structure of the product through interpretation of the IR spectrum. Pelter, Michael W.; Macudzinski, Rebecca M.; Passarelli, Mary Ellen. J. Chem. Educ.2000, 77, 1481.

IR Spectroscopy |

Microscale Lab |

Alcohols |

Oxidation / Reduction |

Molecular Properties / Structure

Time-Dependent Changes in a Shampoo BubbleArun ChattopadhyayThis article demonstrates the fascinating phenomenon of time evolution of a shampoo bubble. The changes in thickness of the bubble films with time are followed by UV-vis spectroscopy. The change in chemical composition as a bubble film evolves is monitored by FTIR spectroscopy. Chattopadhyay, Arun. J. Chem. Educ.2000, 77, 1339.

Photochemistry of Chloropicrin. A Physical Chemistry ProjectE. A. Wade, T. P. Clemes, and K. A. SingmasterIn this experiment, students will use FTIR spectroscopy to monitor the kinetics of the photolysis of chloropicrin by an Hg arc lamp, both with and without oxygen. They will then be able to determine the mechanism of the photolytic reaction. Wade, Elisabeth A.; Clemes, T. P.; Singmaster, Karen A. J. Chem. Educ.2000, 77, 898.

Studying Thermally Induced Chemical and Physical Transformations in Common Synthetic Polymers: A Laboratory ProjectSteven C. Hodgson, John D. Orbell, Stephen W. Bigger, and John ScheirsA simple project is described for introducing students to some experimental procedures commonly used to measure the effects of thermal treatment on synthetic polymers. The thermally induced changes that occur in the commodity polymers low-density polyethylene (LDPE), poly(ethylene terephthalate) (PET), and poly(vinyl chloride) (PVC) are examined as a function of the time of thermal treatment in an air-circulating oven.Hodgson, Steven C.; Orbell, John D.; Bigger, Stephen W.; Scheirs, John. J. Chem. Educ.2000, 77, 745.

Reaction of Dibenzoylethylene with Hydriodic AcidFred H. GreenbergDibenzoylethylene is treated with hydriodic acid in acetone at room temperature to obtain dibenzoylethane rather than the expected dibenzoyliodoethane. Students identify the product by the use of NMR and IR spectra and are given a nonpictorial representation of a mechanism and asked to supply the structures of the relevant intermediates. Greenberg, Fred H. J. Chem. Educ.2000, 77, 505.

Microscale Lab |

Synthesis |

NMR Spectroscopy |

IR Spectroscopy |

Mechanisms of Reactions |

Reactive Intermediates

Molecular Modeling to Predict Regioselectivity of Hydration ReactionsKate J. Graham, Kathleen Skoglund, Chris P. Schaller, William P. Muldoon, and John B. KlassenStudents oxidize several isomeric alkenes using acid-catalyzed hydration, oxymercuration/demercuration, and hydroboration to compare the regioselectivity of the different techniques. The product mixtures are subsequently analyzed by GC and IR. To explain the results fully, students use the Spartan 5.0 molecular modeling package to predict the regioselectivity of these hydration reactions. Graham, Kate J.; Skoglund, Kathleen; Schaller, Chris P.; Muldoon, William P.; Klassen, John B. J. Chem. Educ.2000, 77, 396.

Multicomponent Reactions: A Convenient Undergraduate Organic Chemistry ExperimentRicardo Bossio, Stefano Marcaccini, Carlos F. Marcos, and Roberto PepinoTwo experiments for the synthesis of a -lactam and a succinimide, based on a 4-component Ugi condensation. The experimental procedures for both syntheses are identical except for the choice of the starting amine, whose electron richness is controlled by the presence or absence of an electron-withdrawing group. Bossio, Ricardo; Marcaccini, Stefano; Marcos, Carlos F.; Pepino, Roberto. J. Chem. Educ.2000, 77, 382.

Identifying Softwoods and Hardwoods by Infrared SpectroscopyBrady Barker and Noel L. OwenInfrared spectra of 45 softwoods and hardwoods have been recorded. The wavenumber values of the carbonyl stretching vibration and one of the ring-breathing modes of lignin are used to distinguish softwoods from hardwoods. The differences between the absorption bands for the softwoods and hardwoods in each instance are shown to be statistically significant. Barker, Brady; Owen, Noel L. J. Chem. Educ.1999, 76, 1706.

Carbohydrates |

Instrumental Methods |

IR Spectroscopy |

Plant Chemistry |

Molecular Properties / Structure

Greenhouse Warming Potentials from the Infrared Spectroscopy of Atmospheric GasesMatthew J. ElrodA model is described that allows a straightforward, spreadsheet-based determination of greenhouse warming potentials from the infrared spectra of atmospheric gases. On the basis of the numerical results of the model, students are able to investigate the molecular properties that are characteristic of greenhouse gases and thus are able to understand the rationale behind the recent agreement by the world's industrialized nations to reduce certain greenhouse gas emissions. Elrod, Matthew J. J. Chem. Educ.1999, 76, 1702.

Gradualism: A Method for Primary Instruction on Spectroscopic Analysis in Introductory Organic ChemistryChristopher W. Alexander, Gary L. Asleson, Charles F. Beam, Marion T. Doig, Frederick J. Heldrich*, and Shannon Studer-MartinezThe pedagogical style of gradualism is described for the instruction of spectroscopic analysis in the introductory organic chemistry laboratory. Gradualism is defined as a series of steps or lessons that build one upon the other until the student is able to solve complex problems. Alexander, Christopher W.; Asleson, Gary L.; Beam, Charles F.; Doig, Marion T.; Heldrich, Frederick J.; Studer-Martinez, Shannon. J. Chem. Educ.1999, 76, 1297.

IR Spectroscopy |

Mass Spectrometry |

NMR Spectroscopy |

UV-Vis Spectroscopy |

Learning Theories

Spectroscopic Instruction in Introductory Organic Chemistry: Results of a National SurveyChristopher W. Alexander, Gary L. Asleson, Marion T. Doig, and Frederick J. Heldrich* The survey results indicated that the spectroscopic techniques of IR, MS, proton NMR, and carbon NMR are core techniques in most courses. A considerable amount of the instruction in spectroscopy is occurring in both the laboratory and the lecture portions of the course.Alexander, Christopher W.; Asleson, Gary L.; Doig, Marion T.; Heldrich, Frederick J. J. Chem. Educ.1999, 76, 1294.

IR Spectroscopy |

Mass Spectrometry |

NMR Spectroscopy |

UV-Vis Spectroscopy |

Spectroscopy

Undergraduate Lectures on Infrared Spectroscopy in the Solid StateE. A. SeccoThis experimental exercise exposes students to the reduction in symmetry for a polyatomic species such as NO3- or SO42- in a crystalline lattice. The experiment illustrates how splitting of degenerate modes occurs and how infrared inactive modes become active. Secco, E. A. J. Chem. Educ.1999, 76, 373.

IR Spectroscopy |

Solid State Chemistry |

Crystals / Crystallography |

Solids

Near Infrared (NIR) Spectroscopy in the Undergraduate Chemistry CurriculumM. Cecilia YappertThe power of NIR spectroscopy is best and most often realized in the study of compounds containing O-H, N-H and C-H bonds. For example, the content of protein, moisture, carbohydrates, and lipids in complex samples can be determined with the use of NIR spectroscopy, without the need for time-consuming extraction steps. Yappert, M. Cecilia. J. Chem. Educ.1999, 76, 315.

IR Spectroscopy |

Quantitative Analysis

Spectroscopy of Simple MoleculesC. Baer and K. CornelyA spectroscopy experiment in which students utilize IR and NMR spectroscopy to identify the structures of three unknowns from a list of 15 carefully chosen simple organic molecules. In taking IR and NMR spectra, students learn to use state-of-the-art instrumentation that is used by practicing chemists. Baer, Carl; Cornely, Kathleen. J. Chem. Educ.1999, 76, 89.

Instrumental Methods |

IR Spectroscopy |

NMR Spectroscopy |

Molecular Properties / Structure

Using Excel Solver: An Addendum to the HCl Infrared Spectrum ExperimentMark IannoneSolver, a flexible and convenient add-in provided with Excel, is useful for fitting of a nonlinear model to experimental data. Solver is introduced to physical chemistry students in the context of the analysis of the fundamental band of the infrared spectrum of gaseous HCl. All peak positions in the P and R branches are used to find least-squares values for the pure vibrational transition, the rotational constants in v = 0 and v = 1 states, and the centrifugal distortion constant. Iannone, Mark. J. Chem. Educ.1998, 75, 1188.

Spectrophotometry (by Barbara Sawrey and Gabriele Wienhausen)reviewed by David PringleSpectrophotometry is an interactive CD-ROM which introduces the basics of UV-visible spectrophotometry with some mention of infrared and other forms of spectrophotometry. The CD is divided into six sections: Introduction, Background, A Detailed Look, The Spectrophotometer, Practice, and Quantitative Spectrophotometry.Pringle, David. J. Chem. Educ.1998, 75, 978.

UV-Vis Spectroscopy |

IR Spectroscopy

Synthesis and Structure-Property Relationships in (h6-Arene)Cr(CO)3 Chemistry: From Guided Experiments to Discovery ResearchAllen D. Hunter, Larry J. Bianconi, Steven J. DiMuzio, and Dianne L. BrahoSince instructors can have each student prepare a different complex, they are ideal targets for student directed "discovery research" lab projects. Teams of students can compare how their syntheses and the physical, spectroscopic, and electrochemical properties of their products vary as a function of the arenes' structures.Hunter, Allen D.; Bianconi, Larry J.; DiMuzio, Steven J.; Braho, Dianne L. J. Chem. Educ.1998, 75, 891.

A Low-Cost Auto-Stop Hydraulic Press for Making KBr DiscPing-Kay HonA hydraulic press fitted with an adjustable torque wrench, together with a stand made of iron bars will form an auto-stop hydraulic press for making KBr disc in IR studies. Total material cost is about $100.Hon, Ping-Kay. J. Chem. Educ.1998, 75, 629.

Laboratory Equipment / Apparatus |

IR Spectroscopy |

Laboratory Management

Incorporating Organic Name Reactions and Minimizing Qualitative Analysis in an Unknown Identification ExperimentClaire Castro and William KarneyThe authors have developed a new type of unknown identification experiment for the introductory organic chemistry laboratory. The unknown sample the student is provided with is the product of an organic name reaction. The student is only informed of the starting material and conditions used in the compound's synthesis, and must then: (1) deduce the compound's structure, (2) determine the name reaction and corresponding mechanism that yields the compound, and (3) present his/her results to the class. Claire Castro and William Karney. J. Chem. Educ.1998, 75, 472.

IR MENTOR PRO 2.0reviewed by John C. CochranIR Mentor Pro:2.0 appears to be the ultimate reference source for infrared spectroscopy of organic molecules. This on-line database contains more than six hundred IR band assignments arising from over two hundred functional groups. Cochran, John C. J. Chem. Educ.1997, 74, 764.

Following Microscale Organic Reactions Using FT-IREms-Wilson, JaniceThe progress of two microscale reactions, the reduction of cyclohexanone with sodium borohydride and the photochemical formation of benzopinacol, was monitored, qualitatively, using FT-IR.Ems-Wilson, Janice J. Chem. Educ.1996, 73, A171.

Microscale Lab |

Aldehydes / Ketones |

Photochemistry |

Oxidation / Reduction |

IR Spectroscopy

Over 100 Years of Research on Cyclopentadienylironcarbonyl Chemistry: Microscale-Integrated Organometallic ExperimentsE. Mocellin, M. Ravera, R. A. Russell, and T. HynsonThis unified microscale laboratory program is intended to build independence, confidence and even adventurousness both in synthesis and instrumental analysis, and to apply these results in a meaningful situation by demanding of the students: interpretation of results, evaluation of data and conclusion reached, reference to the original literature, and suggestion of further experimentation. Mocellin, E.; Ravera, M.; Russell, R. A.; Hynson, T. J. Chem. Educ.1996, 73, A99.

Organometallics |

IR Spectroscopy |

NMR Spectroscopy |

Microscale Lab |

Instrumental Methods |

Electrochemistry

IR Spectroscopy Using Disposable Polyethylene Cards: A Replacement for KBr Pellets and MullsLarry S. Wigman, Elizabeth E. Hart, and Constance GombatzDisposable IR cards are a simple alternative to KBr pellets and mineral oil mulls for the analysis of soluble compounds. These cards are commercially available from 3M. The film thickness is reproducible enough to allow for compensation in dual beam instruments or spectral subtraction in single beam instruments.Larry S. Wigman, Elizabeth E. Hart, and Constance Gombatz. J. Chem. Educ.1996, 73, 677.

Use of the Disposable IR Card in the Organic Chemistry LaboratoryHarriet P. Moeur and Robert P. PinnellInfrared spectra of solid and high-boiling liquid compounds can now be observed using Disposable IR Cards. This article reports on their use in the Organic Chemistry classroom. Moeur, Harriet P.; Pinnell, Robert P. J. Chem. Educ.1996, 73, 371.

A Low-Cost Matrix Isolation Experiment: For the Undergraduate LaboratoryMark Flair and T. Rick FletcherMethod for generating and observing the reaction intermediate formed by photolysis of Cr(CO)6 in a low temperature solid matrix illustrating some of the principles of photochemistry and the relationship of spectroscopy to molecular structure.Flair, Mark; Fletcher, T. Rick. J. Chem. Educ.1995, 72, 753.

A Qualitative Experiment for Organic Chemistry LabHermann, Christine K. F.This experiment was introduced near the end of second semester. The students were told that the unknowns were either an alcohol, a carboxylic acid, an amine, an aldehyde, or a ketone. The identifications were based on melting points or boiling points, the IR and NMR spectra, and a set of four classification tests.Hermann, Christine K. F. J. Chem. Educ.1994, 71, 991.

The isolation of sesquiterpenes from Artemisia annuaRoth, Ronald J.; Acton, Nancy.Artemisia annua is a Eurasian import in North America and has been found growing in diverse parts of the United States. Procedures have been reported for the isolation of arteannuin B and of arteannuic acid.Roth, Ronald J.; Acton, Nancy. J. Chem. Educ.1989, 66, 349.

An infrared salt plate cleaning deviceHiegel, Gene A.A simple device for holding a salt plate while rinsing it with solvent can be made from a small funnel and a bottle.Hiegel, Gene A. J. Chem. Educ.1987, 64, 261.

Spectroscopy in organic chemistry at the introductory levelGurst, Jerome E.This author has found that the use of a limited series of compounds allow students to focus attention on the spectra rather than the structural formulas of many compounds. This allows students to grasp the significance of the spectral measurements in a minimal time period.Gurst, Jerome E. J. Chem. Educ.1981, 58, 511.

A laboratory exercise for organic chemistrySands, Richard D.Students analyze a mixture of two unknown liquids, which as the semester progresses they are to separate, analyze, and identify.Sands, Richard D. J. Chem. Educ.1975, 52, 732.

Gas Chromatography |

Separation Science |

IR Spectroscopy

The preparation and spectral analysis of toluene-a[alpha]-dEllis, Jerry W.; Buchanan, David H.Provides dramatic visual evidence of the changes in IR, NMR, and mass spectra upon substitution of deuterium for hydrogen in a simple molecule.Ellis, Jerry W.; Buchanan, David H. J. Chem. Educ.1975, 52, 265.

Use of infrared spectrophotometry in the analysis of limestoneKalbus, Gene E.; Kalbus, Lee H.This paper reports an exploration and extension of the usefulness of infrared as a teaching aid in the field of inorganic analytical chemistry. Includes sample spectra and their analysis.Kalbus, Gene E.; Kalbus, Lee H. J. Chem. Educ.1966, 43, 314.

Infrared spectroscopy: A chemist's toolPimentel, George C.This paper serves as an introduction to infrared spectroscopy and seeks to explain why it has assumed such an important role in chemistry.Pimentel, George C. J. Chem. Educ.1960, 37, 651.